Flights from Chicago to Westchester County (MDW → HPN)

MDW
Chicago
Chicago Midway International, USA
HPN
Westchester County
Westchester Co, USA
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No direct flights found. Here are the 17 fastest 1-stop options.
viaDetroit(DTW)
MDW→DTW+1h 30mDTW→HPN
2h 53m
viaWashington(DCA)
MDW→DCA+1h 30mDCA→HPN
3h 5m
viaRaleigh/Durham(RDU)
MDW→RDU+1h 30mRDU→HPN
3h 33m
viaCharlotte(CLT)
MDW→CLT+1h 30mCLT→HPN
3h 40m
viaMyrtle Beach(MYR)
MDW→MYR+1h 30mMYR→HPN
4h
viaAtlanta(ATL)
MDW→ATL+1h 30mATL→HPN
4h 6m
viaMinneapolis(MSP)
MDW→MSP+1h 30mMSP→HPN
4h 6m
viaCharleston(CHS)
MDW→CHS+1h 30mCHS→HPN
4h 10m
viaSavannah(SAV)
MDW→SAV+1h 30mSAV→HPN
4h 21m
viaJacksonville(JAX)
MDW→JAX+1h 30mJAX→HPN
4h 44m
viaOrlando(MCO)
MDW→MCO+1h 30mMCO→HPN
5h 14m
viaTampa(TPA)
MDW→TPA+1h 30mTPA→HPN
5h 20m
viaSarasota(SRQ)
MDW→SRQ+1h 30mSRQ→HPN
5h 30m
viaFort Myers(RSW)
MDW→RSW+1h 30mRSW→HPN
5h 41m
viaFort Lauderdale(FLL)
MDW→FLL+1h 30mFLL→HPN
5h 48m
viaMiami(MIA)
MDW→MIA+1h 30mMIA→HPN
5h 51m
viaSan Juan(SJU)
MDW→SJU+1h 30mSJU→HPN
8h 29m
Search all options on Kiwi.com → Total times include an estimated 90-minute layover. Actual times vary by airline and connection.

Frequently asked questions

Are there direct flights from Chicago to Westchester County? Currently, there are no direct flights from MDW to HPN. You may need to connect through another airport.

Related guides for this route

Sibling pages from across Flightmaps — fares, visa rules, country aggregations, and per-airline routes for Chicago → Westchester County.

Cheap flights from Chicago to Westchester County Cheapest month to fly to Westchester County Flights from USA Flights to USA Visa-free with USA passport All airports in USA

Try a nearby airport to Chicago

Flights to Westchester County (HPN) from other airports within 350 km of Chicago. Often unlocks cheaper fares or better times.

ORD → HPN 25 km from MDW Chicago → Westchester County USA · 282 destinations SBN → HPN 119 km from MDW South Bend → Westchester County USA · 22 destinations RFD → HPN 121 km from MDW Rockford → Westchester County USA · 8 destinations MKE → HPN 130 km from MDW Milwaukee → Westchester County USA · 34 destinations BMI → HPN 175 km from MDW Bloomington → Westchester County USA · 6 destinations

Or try a nearby airport to Westchester County

Flights from Chicago (MDW) to other airports within 350 km of Westchester County.

MDW → LGA 36 km from HPN Chicago → New York USA · 92 destinations MDW → JFK 48 km from HPN Chicago → New York USA · 201 destinations MDW → EWR 58 km from HPN Chicago → New York USA · 189 destinations MDW → SWF 58 km from HPN Chicago → Newburgh USA · 8 destinations MDW → ISP 60 km from HPN Chicago → Islip USA · 16 destinations

Other flights from Chicago (MDW)

Aguascalientes (AGU) Albany (ALB) Albuquerque (ABQ) Asheville (AVL) Atlanta (ATL) Austin (AUS) Baltimore (BWI) Birmingham (BHM) All 97 destinations →

Other flights from Westchester County (HPN)

Atlanta (ATL) Bermuda (BDA) Charleston (CHS) Charlotte (CLT) Chicago (ORD) Daytona Beach (DAB) Detroit (DTW) Fort Lauderdale (FLL) All 26 destinations →